Potassium Carbonate → 2-methyl-5-nitro-6-(4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-3H-pyrimidin-4-one

HRID 841017Notes

Reaction equation

HRID 841017 reaction equation
Br[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[N+:10]([O-:12])=[O:11].[S:13]1[C:22]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17][C:16]=2[N:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:8][C:6]1[NH:5][C:4](=[O:9])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([N:19]2[CH2:20][CH2:21][C:22]3[S:13][CH:14]=[N:15][C:16]=3[CH2:17][CH2:18]2)[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 226207475,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepineHCID 1356171936-bromo-2-methyl-5-nitro-3H-pyrimidin-4-one

Product 1

HCID 1356711552-methyl-5-nitro-6-(4,5,7,8-tetrahydro-thiazolo[4,5-d]azepin-6-yl)-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure described in example 1c 6-bromo-2-methyl-5-nitro-3H-pyrimidin-4-one (example 1a) was treated with the 5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine in N,N-dimethylformamide in the presence of potassium carbonate at room temperature to yield the 2-methyl-5-nitro-6-(4,5,7,8-tetrahydro-thiazolo[4,5-d]azepine-6-yl)-3H-pyrimidin-4-one as yellow amorphous solid; MS: (M−H]−=306.

Sources & evidence

ORD record
ord-66daebd3d24c4bcb8121f99ebe93eb38
Source dataset
uspto-grants-2002_04
Patent number
US06369222B1

Reaction notes

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